Delta3-tetrahydrobenzaldol



Patented Feb. 24, 1948 A -TETRAHYDROBENZALDOL Joseph E. Bludworth,Corpus Christi, Tex., and Donald P. Easter, Washington, D. C., assignorsto Celanese Corporation of America, a corporation of Delaware NoDrawing. Original application January 22,

1944, Serial No. 519,352. Divided and this application April 25, 1946,Serial No. 664,981

1 Claim. 1

This invention relates to novel organic compounds and relates moreparticularly to A -tetrahydrobenzaldol and to the derivatives thereof.

This application is a division of United States Application S. No.519,352, filed January 22, 1944, now Patent No. 2,410,007.

An object of our invention is the preparation of M-tetrahydrobenzaldol.

Another object of our invention is the utilization ofM-tetrahydrobenzaldol as an intermediate in the synthesis of variousorganic compounds.

Other objects of our invention will appear from the following detaileddescription.

The reaction of acroiein with butadiene in accordance with theDiels-Alder condensation yields A -tetrahydrobenzaldehyde,

CH; O C CHC H H H:

This cyclic aldehyde is quite reactive and, as a starting material maybe employed as a fertile source of novel and valuable synthetic organicmaterials.

We have now discovered that the aldol condensation of A-tetrahydrobenzaldehyde yields the aldol condensation product A-tetrahydrobenzaldol having the following structural formula:

II C-H al i f? -o--cn n CH (3H3 AH (BE: /CH

C a CH:

are employed and, preferably, the alkali is added in the form of asolution in a suitable organic solvent, e. g. ethyl alcohol or the like.The A tetrahydrobenzaldehyde is placed in a suitable vessel equippedwith a stirrer and the alkali solution added slowly while the mixture isstirred.

The condensation to A -tetrahydrobenzaldol takes place rapidly with theevolution of heat. The temperature is maintained below about C. duringthe condensation by applying suitable cooling means and, at thecompletion of the condensation, the polymer is obtained in the form of aliquid. The aldol is washed twice with an equal volume of water. Thewater layer is discarded, and'the aldol is taken up in twice its volumeof ether. The ether solution is dried with anhydrous sodium sulfate andfiltered. The resulting mixture is heated to drive off the ether.

In order further to illustrate our invention but without being limitedthereto the following example is given:

Example 400 parts by weight of A -tetrahydrobenzaldehyde, prepared bythe Diels-Alder condensation of acroiein and butadiene, are placed in avessel equipped with a suitable stirrer and a saturated solution ofsodium hydroxide in ethyl alcohol is added slowly with constantstirring. The temperature rises during the condensation but is keptbelow about 65 C. during the course of the reaction. The productobtained comprises A3- tetrahydrobenzaldol.

The valuable A -tetrahydrobenzaldol may also be oxidized to yield highmolecular weight acids which may be employed in the synthesis of variousother high molecular weight derivatives.

It is to be understood that the foregoing detailed description is givenmerely by way of illustration and that many variations may be madetherein without departing from the spirit of our invention.

Having described our invention, what we desire to secure by LettersPatent is:

As a new compound, A -tetrahydrobenzaldol,

JosEPH E. BLUDWORTH. DONALD P. EASTER.

REFERENCES CITED The following references are of record in the file ofthis patent:

Bate, The Synthesis of Benzene Derivatives, page 192 (1926).

Diels et al., Liebigs Annalen der Chemie, vol. 460, pages 98-122 (1928).

